Research suggests that men may experience distress in ways that go undetected. Many commentators argue that hegemonic forms of masculinity can render men unable or unwilling to deal constructively with distress, leading to maladaptive responses including avoidant behaviour and emotional numbing. However, there are indications in the research that men are also able to constructively engage with their well-being, although little research exists exploring how they do so. The present study sought to find men who currently appear to self-manage their well-being in order to examine issues around how men adopt a constructive approach. In-depth narrative interviews were conducted with 30 male meditators in the UK, selected using principles of maximum variation sampling. Using a modified grounded theory approach, the analysis suggests that while these men took up meditation for varying reasons, they have discovered strategies to better manage their wellbeing. However, the journey towards meditation was fraught with difficulties. Men described crossing a threshold from boyhood into ‘manhood’, and most had tried in the past to be emotionally tough and/or disconnect from difficult emotions. Many had experienced internal conflict, and sought relief in a variety of ineffectual coping responses. Exploring varying pathways toward meditation, this study sheds light on the ways men deal with distress and find constructive ways of coping. Here, resisting dominant norms of masculinity is a difficult struggle for men. Moving away from the ‘masculinity as deficit’ model, we discuss implications for helping men to better understand, engage with, and manage their feelings of distress.